Synthesis and spectral characteristics of N-(2,2,2-trichloro-1-((5-(R-amino)-1,3,4-thiadiazol-2-yl)amino)ethyl)carboxamides

In this paper, we reported the development of an efficient and highly productive synthetic protocol for preparing new 2,5-diamino-1,3,4-thiadiazole derivatives functionalized with N-(2,2,2-trichloroethyl)carboxamide group. The method of their preparation was based on the reaction of oxidative dehydrosulfurization of N-(2,2,2-trichloro-1-(2-(phenylcarbamothioyl)hydrazine-1-carbothioamido)ethyl)­carboxamides and N-(1-(2-carbamothioylhydrazine-1-carbothioamido)-2,2,2-trichloroethyl)benzamide under the action of a mixture of iodine and triethylamine in DMF. This reaction took place at room temperature for two hours and allowed obtaining the target products with a 69-75% yield. Using the developed protocol, we obtained ten new derivatives of 1,3,4-thiadiazole. Their structure was proven by IR,¹H NMR,¹³C NMR, ¹H-¹H COSY, ¹H-¹³C HSQC, ¹H-¹³C HMBC spectroscopy, and LC/HRMS spectrometry.